By Dr. Michael Cullinane and Chris Cosentino
The majesty of the copper buttes and mighty figure of the American bison provided the backdrop for the 107th Annual Meeting and the first-ever Theodore Roosevelt Convention (#TeddyCon). Sunshine lit the Theodore Roosevelt Presidential Library, giving the weekend the feel of a cool summer day. Attendees arrived in droves – more than 270 friends – to a packed program of scholars, entertainers, and keynote speakers, culminating in a live podcast of Talk About Teddy. Each day had a common rhythm: talks in the auditorium in the morning gave way to guided activities in the afternoon: to Theodore Roosevelt National Park, the Elkhorn unit, and through the museum with experts. In the evening, we returned to the auditorium for talks and entertainment, separated by dinner alongside the rammed earth walls in the library’s lobby.
Each element of the program stood out around the theme “Looking Back, Moving Forward.” #TeddyCon was a collaborative event between the TRA and the Theodore Roosevelt Center at Dickinson State University highlighting the strong partnership between the two organizations.
“The Theodore Roosevelt Association extends its sincere gratitude to our partners at the Theodore Roosevelt Center at Dickinson State University and the Theodore Roosevelt Presidential Library, as well as everyone who helped make this historic gathering possible,” said Chris Cosentino, Executive Director of the Theodore Roosevelt Association. “A special thank you to TRA’s Public Historian and Co-Director of the Theodore Roosevelt Center, Dr. Michael Cullinane, for his outstanding efforts in curating such a remarkable program. We are already looking forward to building on this momentum at next year’s event in New York!”
“#TeddyCon exceeded my expectations,” said the TRA’s Public Historian Michael Cullinane, “The weekend brought together many great parts of the TR universe and celebrated in style. I cannot thank our partners enough for turning out and making the convention a rollicking triumph.”
The authors’ panel on Friday brought world-famous biographers together to discuss motives, perspectives, and interpretations in the history books. Moderated by Craig Blumenshine, the panel included Dr. Kathleen Dalton, Dr. Lindsay Chervinsky, and Dr. Stacy Cordery. The fact that all these writers are women was not lost on the audience. Questions about the growing body of scholarship produced by female biographers mixed with questions about whether women have a unique perspective when writing about men. Dr. Dalton and Dr. Cordery have written extensively about Theodore Roosevelt, which allowed the conversation to delve into his reception among authors. Dr. Chervinsky provided a broader context as the biographer of early American presidents. All the participants weighed into debates on presidential scholarship and how the traditions of the executive branch resonate in contemporary debates.
Lunch each day was taken in the breezeway – a covered space between the east and west wings of the Library – where a gentle wind enhanced the revelry. We could not have wished for better weather. October in North Dakota is unpredictable. It could have as easily dipped below freezing, but the Gods smiled on the attendees. Temperatures hit 85 degrees on Friday and 80 degrees on Saturday. Sunday dipped into the 50s, suggesting that we squeezed the last of the summer warmth from the Badlands.
After lunch each day attendees could take in the popular exhibition space featuring 15 stellar exhibitors and sponsors. Alternatively, visitors could opt to take a bus tour of the nearby TR National Park with Valerie Naylor, the park’s former superintendent. Or they could tour the Library with Michael Cullinane and Susan Sarna. Or they could drive to the Elkhorn Ranch for a tour with Dr. William Hansard of the TR Center. Short of these fantastic tours, a visitor could take in Medora and all it has to offer.
Friday’s keynote session featured journalist and politician John Avlon in conversation with the TRA’s public historian Michael Cullinane. The topic was TR’s most famous speech: Citizenship in a Republic, better known as the Man in the Arena speech. Delivered in Paris, at the Sorbonne in 1910, the speech has taken on a contemporary relevance. Sports stars, celebrities, and politicians invoke it regularly. Avlon explained when it became popular (in the 1950s) and how the internet age has increased its popularity. The discussion covered much more, and the recordings of all the sessions are available on the TRA’s social media.
We closed Friday with a showcase of White House Princess, featuring several songs in the production. Written by TRA members Maureen Clare and Charlotte Daniels, the musical explores the life of Alice Roosevelt and her relationship with Eleanor Roosevelt, who were cousins and defining characters of their generation. Songs about “lavender love” and TR’s relationship with both women combined with the piano recitals of the writers and made for an exciting end to the first day. During the showcase, they highlighted their extensive research, drawing on years of work at Harvard University’s Houghton Library with Christine Jacobson and at Sagamore Hill, as well as personal conversations with Alice Roosevelt’s granddaughter, Joanna Sturm. Special thanks to performers Isa Pena (Alice), Emma Rogers (Eleanor), and Mack Webb (Theodore Roosevelt).
Saturday began in the same fashion: a video message from TRA Trustee and Congressman French Hill, a State of the Field address from Dr. Michael Cullinane, a fun TR-Trivia Contest hosted by repriser Joe Wiegand, and another panel of experts. This session focused on the Badlands and featured TRA regular Duane Jundt, former mayor of Medora Doug Ellison, and historian Rolf Sletten. Moderated by Joe Weigand, who lives in Medora, the session allowed the audience a deep insight into the town and the wider region. The panelists talked about the birds that TR saw in the Badlands, the friends Roosevelt made, and the interesting episodes of the 1880s and beyond.
Like Friday, lunch and guided tours followed the morning panel. Then, in the evening, the attendees returned for a keynote lecture and conversation with Karl Rove. As President George W. Bush’s senior White House advisor, Rove has a unique insight into the way the presidency operates. He also authored a book about the election of 1896 and McKinley’s administration, which was the basis of his lecture. For thirty minutes, Rove spoke about TR as a political animal that resuscitated his career by gaining the trust of McKinley. After the lecture, Talmage Boston, a friend of Rove’s and a Dallas lawyer, discussed the finer points of the era.
After a dinner, the group returned for the TRA Awards Ceremony which featured a powerful message from Scott Cooper, SVP Government Affairs at the nonprofit organization With Honor, which was #TeddyCon’s generous Legacy Sponsor. The Awards Ceremony continued with the Executive Director of the National War College Alumni Association, Michael Prosser, who bestowed the Theodore Roosevelt Award on Foreign Service Officer Rob McCutcheon, who also provided an inspiring address to attendees. VADM David Architzel closed the Awards Ceremony with a rousing address discussing the relationship between the Theodore Roosevelt Association and the currently deployed, USS Theodore Roosevelt (CVN-71). VADM Architzel introduced a video from aboard “The Big Stick” featured Captain William Mathis and the TRA’s 2026 Junior Officer of the Year, LT Jonathan Cipoletta.
Following the awards ceremony, attendees were treated to a special performance by singer-songwriter and American Idol alumnus Mason Via. Via’s masterful fretwork filled the auditorium with notes of bluegrass, blues, and Appalachian folk music. He finished his set with the 2026 hit single “See It While You Can (National Parks Song),” a tribute to public lands and national parks that mentions “Mr. Roosevelt” as the progenitor of the conservation movement. The performance featured a rendition of Woody Guthrie’s iconic “This Land Is Your Land,” inspiring the audience to sing along and culminating in a standing ovation. Via was also joined by acclaimed harmonica player Corey Flick, who accompanied him on two songs, adding another dynamic element to the memorable performance.
The hardcore attendees had the added benefit of Sunday and the live podcast of Talk About Teddy with its hosts Larry Marple and Kurt Skinner. Michael Cullinane and Susan Sarna joined the hosts for a 90-minute conversation about how the exhibits at the TR Presidential Library came into existence. What was left on the drawing room floor provided an insight into how the museum took shape.
Before the party ended midday on Sunday, and the exhibitors packed up, the hosts took a moment to thank the crowd and each other. The TRA and the TR Center did something remarkable in Medora. They had a blowout party for TR and his new Library. Those who made it are unlikely to forget it for some time.
We look forward to welcoming everyone to the Theodore Roosevelt Association's 108th Annual Meeting in New York City and Oyster Bay next October! Stay connected to www.theodoreroosevelt.org for more information when it becomes available.